Bertie Wooster tells Jeeves about his first experience of sex with a woman

Grok: Setting: Bertie Wooster’s plush London flat, April 2025. Bertie is fidgeting nervously on a leather armchair, clutching a gin and tonic like it’s a life preserver. Jeeves, ever the picture of unruffled composure, is polishing a silver cigarette case with a cloth, his expression as inscrutable as a sphinx.
Bertie: I say, Jeeves, I’ve got myself into a bit of a pickle. Well, not a pickle exactly—more of a… a dashed awkward situation. Gulps drink. You see, last night at the Drones Club, after one too many of those new-fangled espresso martinis, I… er… had my first, ahem, encounter with a woman. And I’m in a frightful muddle about it!
Jeeves: Pausing mid-polish, eyebrow barely twitching. Indeed, sir? A significant milestone, if I may say. Might I inquire as to the circumstances, so as to better advise you on the matter?
Bertie: Circumstances? Oh, it’s a dashed blur, Jeeves! There was this girl—Poppy Pendleton, frightfully modern, wears those sparkly frocks that look like they’re made of disco balls. We were chatting about, I don’t know, drone racing or some such rot, and next thing I know, we’re in a cab to her flat in Shoreditch. And then… well… blushes crimson things happened. Things I shan’t describe, lest I turn the color of a beetroot!
Jeeves: Calmly resuming polishing. I quite understand, sir. Discretion is paramount. May I infer that the experience has left you somewhat unsettled?
Bertie: Unsettled? Jeeves, I’m a positive wreck! I mean, it was all very… er… thrilling, in a way, but now I’m terrified Poppy’s going to show up at my door demanding I propose or, worse, tweet about it on X! You know how these modern girls are—always posting their breakfasts and their feelings. What if I’m trending as “Bertie the Bungler” by teatime?
Jeeves: A valid concern, sir, given the proclivities of social media. However, I suspect Miss Pendleton’s intentions may be less matrimonial or public than you fear. If I might venture, was the encounter consensual and conducted with mutual respect?
Bertie: Oh, absolutely, Jeeves! I’m no cad. Poppy was all for it—kept calling me “darling” and giggling like a schoolgirl. But that’s just it—she’s so forward! What if she expects me to be her steady beau now? I’m not cut out for romance, Jeeves. I’m a fellow who likes his eggs sunny-side up and his evenings free of emotional entanglements.
Jeeves: Placing the cigarette case on a side table. A prudent stance, sir. To navigate this delicate situation, I would suggest a tactful follow-up with Miss Pendleton to ascertain her expectations. A polite message—perhaps via text, given the contemporary context—could clarify matters without committing you to undue obligations.
Bertie: A text? Me? Jeeves, I can barely manage emojis without sending a peach when I mean a thumbs-up! And what would I say? “Jolly good show last night, but let’s not make it a habit”? She’ll have my head on a platter, or worse, screenshot it for her followers!
Jeeves: Suppressing the faintest smirk. I could draft a suitable message, sir, designed to convey gratitude and goodwill while gently establishing boundaries. For instance: “Dear Poppy, thank you for a delightful evening. I trust we shall remain the best of friends. Yours, Bertie.” This strikes a cordial note without inviting further entanglements.
Bertie: Brightening slightly. By Jove, Jeeves, you’re a genius! That sounds just the ticket—friendly, but not so friendly I’m picking out engagement rings. But what if she does want more? I mean, she was awfully keen—kept saying I had “potential,” whatever that means. Sounded like something you’d say about a racehorse.
Jeeves: Thoughtfully. The term “potential,” sir, may reflect Miss Pendleton’s enthusiasm rather than a demand for commitment. Modern sensibilities often favor casual liaisons over binding contracts. Nevertheless, should she press for a deeper connection, you might gently cite your dedication to a life of unencumbered bachelorhood.
Bertie: Unencumbered bachelorhood! That’s me to a T, Jeeves! Why, I’d rather face Aunt Agatha’s wrath than get roped into picnics and pet names. Still, I can’t stop replaying the whole thing in my head. It was… well, dashed educational, but I’m not sure I’m built for this sort of caper. Too much like trying to dance a foxtrot during an earthquake.
Jeeves: Nodding sagely. A vivid metaphor, sir. Such experiences, while initially disorienting, often contribute to one’s personal growth. Should you wish to avoid future quakes, I could advise on strategies to maintain platonic relations at the Drones Club—perhaps limiting your intake of espresso martinis.
Bertie: Laughing nervously. Limit martinis? You’re pulling my leg, Jeeves! But you’re right—I got carried away. Poppy’s a corker, but I’m not ready to be anyone’s leading man. Draft that text, will you? And maybe pour me another G&T to steady the old nerves. This modern love business is more perilous than a round with Gussie Fink-Nottle’s newt obsession!
Jeeves: Very good, sir. He glides to the bar, then pauses. If I may, sir, you have navigated this rite of passage with commendable, if inadvertent, aplomb. I shall ensure Miss Pendleton receives a message of utmost tact, preserving both your dignity and your liberty.
Bertie: Sinking back into the chair, relieved. Jeeves, you’re a marvel. A positive marvel. Here’s to liberty, gin, and never trending on X!
Jeeves: Pouring the drink with a ghost of a smile. To liberty, sir. He hands Bertie the glass and retreats to compose the text, leaving Bertie to sip and muse on the perils of modern romance.